Group Coaching with Cailen Ascher, Business Coach and Founder, Cailen Ascher International, LLC

About this episode:

Cailen Ascher is an award-winning Business Coach with a 3-day workweek, a mom of two little girls and the creator of Scale-Up Accelerator™ — a program that teaches coaches and online service providers how to create a highly profitable Premium Group Program so they can double revenue while decreasing work hours.

Cailen has been featured in Business Insider, Huffington Post and Inspired Coach Magazine and has been interviewed on top podcasts like Entrepreneurs on Fire and She Means Business Podcast among many others. She is also host of The Soulful Business Show™ which airs weekly. Her programs have helped 1000s of coaches & service providers transform their lives and businesses with her proven strategies for working less, making more and living better.

Topics Discussed:

  • Why Cailen believes staying aligned with her values is crucial for leadership

  • How she helps her clients sustain and transition their coaching business into group offerings

  • Why she believes success is not one-dimensional

  • How she transitioned into a three day work week


About Cailen:

Cailen Ascher is an award-winning Business Coach with a 3-day workweek, a mom of two little girls and the creator of Scale-Up Accelerator™ — a program that teaches coaches and online service providers how to create a highly profitable Premium Group Program so they can double revenue while decreasing work hours.

Cailen has been featured in Business Insider, Huffington Post and Inspired Coach Magazine and has been interviewed on top podcasts like Entrepreneurs on Fire and She Means Business Podcast among many others. She is also host of The Soulful Business Show™ which airs weekly.

Her programs have helped 1000s of coaches & service providers transform their lives and businesses with her proven strategies for working less, making more and living better.

Cailen lives in Bucks County, Pennsylvania with her husband, two young daughters and a spunky dog named Olive.

Get her free training! The High-Five Formula includes a video and workbook that walk you through the 5 essential pillars of a Premium Group Program. Grab it here: www.CailenAscher.com/highfive

Read a raw, unedited transcript of this episode:

Thank you for joining us. You manage and run a six figure business and work just three days a week while also being a hands on mom. Tell us about your business, how you were able to do it and why it is important to you.

Thanks for having me on the show, Melanie. So I have been a business coach since 2015 and the business has transitioned over the years, as I'm sure any woman has been in business a while, I can tell you. But what we're focusing on recently and where we specialize is helping coaches create premium group programs. So this is something that's really near and dear to my heart after having two babies and trying to also do 1 to 1 coaching. And my schedule was filled with calls and it just did not feel sustainable for me. I was so fortunate to be a member of other women's group programs and masterminds, and I realized I actually preferred being coached in a group container with peers that were on the rise and an amazing mentor to guide me. And that's what really lit that light bulb for me, that, hey, I could do this too. And so I've had my own group program since 2018, and then within that started transitioning to teaching women how to build them for themselves. Because a lot of us had a point where the 1 to 1 model just isn't sustainable anymore. Mm hmm.

Good for you. And it was probably helpful to see other women within the group where the situation was relatable. when you have kids, if you're career driven and, all of a sudden, your whole world shifts, seeing other women going through all those struggles is so empowering and inspiring at times.

Yeah. And seeing them navigate it with such grace and poise and then also having moments where things aren't all great and that they're being really vulnerable and real about it. Because if you're just in the world of social media, you never have the full story. And it's so easy to think that everyone's life and business is so much better and more glamorous than your own.

That's so true. What is your approach to leadership, managing your teams and what do you think is the most crucial element of leadership?

What really stands out and what came through when you asked is being values aligned with the people you're working with and the people that you were leading. I'm really clear that I value my family and my time with my family and yes, I want a successful business, but not at the expense of those things that I hold most near and dear to my heart. And that draws in the right people into my world. 99.9% of the time and allows me to be authentic with them, because it's not just all about building a super successful business, which I absolutely love helping them to do, but also having a life they love as well. Because I don't think success is this one dimensional thing that's just about money. it has a different flavor for everyone, and it's really important to know what that looks like for you. And so that's something that I've really stepped into and owned is just being really clear with what I stand for and I find that the right people find you when you do that.

That's so true. And sometimes we think, Oh, if I hit this big revenue goal, then I'll be happy. But what did it take to get there? And, is that balance right for you?

Absolutely. Yeah. And often once you get there, you've been working so hard for it and it just feels kind of normal that what you thought it was going to feel shiny and amazing and new and exciting, and you get there and you're like, all right, I'm here. What's next? Right? Why are we saying goodbye to one on one coaching the best decision you've made for yourself, your family, and your business? And tell us about that transition for someone that might be one on one coaching right now and might want to make the move to group coaching. How did you do that?

Yeah, so it was absolutely the right decision for me for a number of reasons. as I mentioned before, it wasn't sustainable that my energy was feeling so depleted I still had my three day work week way back then, but it was filled with client calls. By the time I got to the end of that third day of back to back calls, I was totally exhausted. This was also right around the time when my girls were really little. I had a two and a half year old and a new baby, and I was like, You know, it's great that I had the six figure coaching business, but I don't really want this business the way it is right now. And so that was a scary realization. And it led me, thankfully, to seek out support for myself. And that's what led me to experience masterminds and group coaching as a member and a participant. And what I found works really well for me and what a lot of women embrace as well when they're working inside my scale up accelerator program is easy, full transition. It's not something where you go in and you're like, I'm firing all my 1 to 1 clients that doesn't feel good at this point, especially because the women I work with and in business a couple of years, usually they're relying on that revenue coming in and they don't want to see it go to nothing and then build from scratch. And so it's really important to have a transition plan and that's something we help all of our clients with. And usually what that looks like is figuring out what is going to sustain you moving forward. And once you find sustainability through the transition and then as you step into the group model, then we can talk about growth and scaling. But to immediately be like, All right, I'm going to jump from 1 to 1 coaching and then the. Exponentially more successful with this new thing that I'm building that's brand new. That's an unrealistic expectation for most of us. And so what we really love is something that feels useful and sustainable, hopefully enjoyable. if you're risk adverse having a planned through that and maybe even hanging on to some of your one on one clients for a time, especially if you love them, that will create a little more space for working on the group model. And then before you know it, this is what happened to me. You're a year or two in and the group programs, the primary flagship offer of the business, bringing in the most revenue of everything when it used to be the 1 to 1 but got to give yourself permission to allow it to take the time it needs to get there. How did you transition to the three day workweek and what does that look like for you today?

Yes. I stepped into my three day workweek when my first daughter was born. So prior to that, I was working longer, more traditional five day workweek, sometimes on the weekends, thinking I had to hustle, work really hard. And that's what will create success in my business. And after she arrived, it's like, you know what? This doesn't feel so good. And if this is what I have to do to be successful and I want to be successful in that way. And so the first experiment was, okay, can I sustain the business? can I sustain the business I was doing in five or six days a week and three days a week? And as I explored how to do that and part of it was getting really clear on my offer, raising my prices to a more sustainable place, instead of under charging and. Getting focused on what I wanted to deliver those clients inside that coaching experience. And I found that within that first year I sustained what I had made. I actually made a little bit more than I'd made the previous year, working five days a week in three days a week, and then the year after that was my first six figure a year. So I proved to myself pretty quickly that your revenue does not have to be tied to the number of hours you're working. That's a huge component of what I love sharing with my clients and teaching and speaking about on podcasts, because It's a real eye opener when we stop thinking that our time equals the money we have to make, and it just blows everything open when we allow ourselves to explore other ways of making money and other ways of thinking about our schedule.

Hmm. So true. And it has to bring so much more joy to your life. Yeah, absolutely.

And it's so healthy to remember that you're more than just your business. As much as I love my business and it's so fulfilling in so many ways and it brings me so much joy. It is separate for me. And so it's good to have time away from it, to have fresh perspective and remember that, there's people and things outside of my office and my desktop that really deserve my time.

What are the mistakes that you see many coaches making when they create a group offering? And how do you suggest they avoid them? Yes. So I would say the biggest mistake I see is they try to layer a group offer on top of their full 1 to 1 schedule or their near full 1 to 1 schedule. They hear somewhere that a group offer is a good idea. This is great. I could sell one thing, they usually have it priced at a lower price point and then I'll move them into my 1 to 1. In theory, on paper, that works great, especially if you have team members and you have people supporting you in managing different aspects of different programs. But if you're solo where it's you want to be a small team that's so much to manage. And often the group program just becomes this headache that you said you were going to deliver. You try to launch it. The launch probably doesn't go quite as you wanted because your schedule is so filled with those clients that you're working with 1 to 1, and you convince yourself it's not going to work for you, or you get stuck delivering this group offer for not enough money because you're probably under charging because you want to price it way less expensive than your 1 to 1 for three people. Like, what did I do here? Why did I take myself into this corner of being stuck with this program that's not working? And so what I love educating women about is thinking of the group offer as the new primary offer of the business, the new signature offer, and not that it has to become that right away, but if that's the direction we're moving in, what are the strategic choices we have to make? And a really big one is how can we create a premium offer, a high ticket offer, not something that's a down sell on a sales call when they're like, No, I don't want to work with you on a one that's too expensive. You're like, Wait, I've got something for $500 you can buy. That doesn't really work, especially if you're going to be delivering it live or giving any of your time to it. And so I think it's really important to go in knowing you're creating a premium experience because then you feel confident pricing it at that premium price point, and then it gives you confidence to let that start to be the thing that drives the revenue in the business.

Such good advice. As a coach, what are the signs to pay attention to that tell you that you're ready to replace your one on one offer with a group program offer?

Yes, there are some red flags to be looking out for. Some of the things I experienced and that I see with my clients who join me inside of my program are that their revenue has plateaued and they're almost scared to try to solve that problem because it means taking on more clients and more work. Their schedule is full up. They feel beholden to their plan or their whatever it is. they wake up in the morning and they see that back to back schedule of fall after call, and they immediately feel exhausted before the day is even done. And their energy and creativity is sapped. It's like I'm giving so much to all of this client work. I'm holding so much space for other people. I've got nothing left for myself. And so if any of those things are all three of those things are starting to appear for you. That's not a sustainable place to be. You have to make adjustments. And not to say creating a group program is the only thing you can do. But what I found was that it freed up my schedule. I went from having back to back calls, ten plus calls a week over those three days to one call a week for my group program definitely freed up my energy because I had that one container to deliver in that one call instead of all of these back to back calls with different clients. And it gave me this capacity to grow my revenue. Instead of feeling capped at ten clients, I could serve even more than that in my group container. And also it opened up other opportunities for collaborations and projects because I had whitespace in my calendar all of a sudden. Even if it's not the group program making all of the money, you might be able to explore other things that generate revenue that you just didn't have time for when your schedule was so full. With client work.

I can see how it can be a little bit scary to make that transition though, especially if they love their clients. But you're right, if you wake up and you're on back to back zooms all day long, or meetings that's going to be exhausting for anyone.

Yes, and it is it can be a scary transition. I remember when I first realized this was the transition I wanted to make. I was like, Well, I can kind of find a client at any time, but now I'm going to have this group program that starts and stops, and I want all of them to start at this time, all of them to end at this other time. And what I realized was a lot of it was mindset that I was getting in my own way I had proven that I had a good thing going. I had worked with dozens and dozens and dozens of clients who paid me highly for the work that I was delivering and every cohort I've had, there has been either a past client that has joined or someone who's re-enrolled and so If you love the work you're doing, this program is an extension of that. sometimes if you were working with, say ten one on one clients, a portion of them might actually want to transition into the group with you. I think sometimes we're scared to ask for like, Oh, they wanted to work with me one on one. They definitely don't want to do this group. We make a decision for them instead of just letting them know, how I can help them, letting them know why we're so excited about making this transition to a group offer and allowing them to make the decision for themselves.

And it might be better because then they can see others like we talked about before going through their similar experiences. And I love the advice to get out of your own way.

Yes. So often we make things harder for ourselves.

We do. We come up with this whole story in our head of what the other person is thinking and feeling. And we're totally projecting. And, if you allow yourself to just be brave and bring up the conversation, sometimes you're surprised by how open and willing and excited they are for the changes that you're making if of course you communicate the benefit for them and all of it so true.

You've built an incredible business and congrats to you for shifting it to three days a week. Really great that you can have that balance with family and still have a business that you love. Please tell our listeners how and where they can find you.

Absolutely. I'd love to connect with you on Instagram. I'm Cailen Ascher that's the social media platform I got on the most. There's lots of fun reels and informative stories and beyond that, http://www.cailenascher.com/ and I have a free gift for everyone. It's called the hi five formula. It's a free training, quick ten-minute video and a workbook to cover the five essential pillars of a premium group program. So if the conversation today got you excited, got you thinking about what a group offer could do for your business. This training is an amazing introduction. They'll start getting the wheels turning to figure out what that could look like for you.


Sabrina Park